


The Unfortunate Life Choices of Dr. Badass

by PessoasLily



Series: Crossroads [5]
Category: Supernatural
Genre: Alternate Universe - Serial Killers, Canon-Typical Violence, Emotional Manipulation, Emotional/Psychological Abuse, Evil Sam Winchester, Gen, Hurt No Comfort, Sam Winchester's Demonic Powers, Serial Killer Sam Winchester
Language: English
Status: Completed
Published: 2017-05-09
Updated: 2017-05-09
Packaged: 2018-10-29 21:46:36
Rating: Mature
Warnings: Graphic Depictions Of Violence
Chapters: 1
Words: 1,491
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/10862718
Author URL: https://archiveofourown.org/users/PessoasLily/pseuds/PessoasLily
Summary: Ash meets Sam Winchester and finds himself at the mercy of a killer.





	The Unfortunate Life Choices of Dr. Badass

**Author's Note:**

> This is a little piece to clear up how Sam knew what he knew and who planted evidence in John's room in [Sam kind of bad as me](http://archiveofourown.org/works/10725060/chapters/23765031)

Ash knew selling his soul was a mistake the day he met Sam Winchester.

He’d been hanging around The Roadhouse playing pool, drinking beer, and shooting the shit with hunters and the Harvelles when Sam walked in. It felt like air had been sucked out of the room. Many of the hunters made excuses about needing to be somewhere else, and a few left out the backdoor before Sam settled himself at the bar. Ellen, bless her soul, smiled at Sam like they were old friends and handed him a beer before he even asked.

Ash had heard rumors, of course. Innuendo and gossip common to outlaws that hunt monsters for a living. Some said he was a murderer. Others said he was the spawn of Satan himself. A few muttered accusations about his relationship with his brother, said it was unnatural. Ash never paid much attention though. He had his own troubles to worry about.

And hunters exaggerated. Everything.

_The vampires fangs were this sharp._

_The werewolf was as big as a bear._

_That witch could brew the balls off a bull._

Stuff like that. It’s hard to take seriously the ramblings of men half crazy themselves.

But that was before Ash got a look at Sam Winchester with his own eyes. He tried not to stare but there was something about him. Something dark and foreboding that crawled into you and made itself at home. If Sam Winchester came with a soundtrack, it’d be something out of a horror film. Jaws or Friday the 13th. Ash always hated those movies.

He was just fixing to leave himself when Sam turned around and stared right at him like he was reading Ash’s mind. Then, excusing himself to Ellen, Sam got up and made a beeline straight for him. Ash isn’t embarrassed to say he almost pissed himself. In spite of Sam’s dimpled smile and shaggy hair, Ash knew it was all true. Sam Winchester was a killer.

And somehow Sam Winchester knew Ash had sold his soul.

As amiable as you please, Sam held out his hand. “Hi, I’m Sam Winchester. I’ve heard a lot about you from Ellen. She tells me you’re quite the computer wiz.”

Ash shook his hand automatically, all his instincts screaming run and hide. 

“That’s right. And I hear you’re John Winchester’s boy.”

Given the look of murder in Sam’s eyes and the way he gripped his hand so tight it hurt, Ash knew that was the worst thing to say. He wasn’t Catholic but he crossed himself internally.

Ignoring him, Sam dropped his hand and said, “Let’s go have a chat.” And with that, he turned and walked out the backdoor, expecting and knowing Ash would follow.

When Ash got outside Sam was leaning against a truck with California plates. It looked old and beat up, poorly cared for. He briefly wondered why someone as powerful as Sam would be driving a piece of shit like that but that was before he saw the body in the cab.

Ash sucked in a breath and Sam just smirked, one eyebrow lifted up in challenge. Ash knew he was meant to ignore the body and did as directed.

“How long ago did you sell your soul,” Sam asked.

“How,” Ash questioned.

“You’re empty on the inside, like a cored apple,” Sam replied, his head titled to the side like he was trying to figure out the best way to dismember him.

“Three years.”

Sam hummed and nodded. “Why?”

“I wanted to learn computers,” Ash replied, not wanting to elaborate.

“That’s what you got out of the deal but that doesn’t tell me why,” Sam said, crossing his ankles and arms, his eyes steady and demanding.

“I just wanted to learn computers, that’s all.”

Sam’s expression turned stormy, his once benign inquiry turning hostile. “Tell me the truth.”

And Ash answered. Like he was compelled. There’s nothing in the world that could stop him from answering.

“I wanted to get out of my shitty trailor park, away from my drunk father and depressed mother. I didn’t want a string of illegitimate babies with women I didn’t love.” Ash clawed at his throat, trying to physically force the words to stop.

Sam nodded as if he was expecting an answer like that.

“What do you know about John Winchester?”

“Nothing. Just what other hunters say. He’s a good hunter. Obsessed with the thing that killed his wife.”

Sam nodded again. Ash wasn’t sure why he asked if he already knew the answer.

“What do you know about me?”

Again, compelled to answer Ash said, “Nothing. Like I said, I just hear rumors. They say you’re a killer. They say you’re a demon. They say Dean does anything you tell him.”

Mentioning Dean was as bad as mentioning John. Sam’s hand flew out and he gripped Ash by the neck, lifting him up off the ground. 

“I’d think twice before saying something like that about my brother.”

Ash grabbed at the hands around his throat, uselessly kicked his legs. His words broken and choked he said, “That’s just what the hunters say.”

Sam dropped him to the ground and Ash scurried backwards in the dirt to get away.

“Going somewhere,” Sam asked, his expression once again amused.

Swallowing around his sore throat, “No. I...I just…”

Sam held up his hand. “Enough. I’ve heard enough.”

Ash nodded and tried to get to his feet, his legs weak and unsteady.

“I’m going to tell you what I want from you and you’re going to do it. Am I understood?”

“Yes, Mr. Winchester. Of course,” Ash agreed. He’d do anything to get out of the presence of this psychopath.

“John is going to be coming to The Roadhouse soon and ask Ellen if she’s seen or heard from me. You’re going to offer your services to track my whereabouts.”

“Why?”

Sam tilted his head again, then lifted his leg and kicked his booted foot into Ash’s knee. Ash crumbled to the ground again. Crying out in pain, Ash begged, “I’m didn’t mean to question you…I...I”

“Stop interrupting me or I’ll break your other leg.”

Ash just nodded and waited.

“He’s going to want you to track me. Instead of tracking me, you’re going to track him. I want every type of surveillance you can think of. Hack his phone, put a tracker on his car. Hack the phones and computers of everyone he contacts, everywhere he goes. I want regular reports of what he’s up to.”

“Sure. Yes. Anything you want.”

Sam kicked him in the stomach.

“I told you to stop interrupting me.”

Ash grimaced in pain and didn’t dare respond in any way, not even a nod.

“He’s going to want to know what I’m doing. You are to tell him nothing but what I tell you to. About me, about my brother. If I detect even the slightest interference in my affairs, I’ll send you to hell myself.”

Ash waited for him to continue. He did.

“John is an unstable man with unhealthy obsessions. You’re going to feed them. I’ll tell you what to tell him, how to direct his path. Am I understood?”

“Yes, Mr. Winchester. Perfectly understood. I will do whatever you say.”

Sam leaned down and grabbed Ash by his short front hair. “I know you will. I’ll also know if you deviate in any way.”

With that, Sam headed back into the bar. Ash fell back into the dirt and waited for someone to find him. When a hunter found him later that evening he told him he’d been attacked by another hunter.

Sam contacted him frequently. Over the phone, by email. He even sent some scary looking people to hand him items. Newspaper clippings of murders. Police and autopsy reports. Things he said he wanted him to give to John when he asked for them. He was told to give John false information about Sam’s whereabouts, apologize when John discovered he was on a wild goose chase. Frustrate his efforts to discover how Sam was tracking him. Ash did as he was told.

When Ash heard that John was staying at The Roadhouse, he told Sam. Sam had one of his men bring him a box and told him to hide it in John’s room. He was told to wear gloves when handling it and make sure Ellen and Jo didn’t see him. Ash did as he was told.

When Ash heard about John’s arrest on TV, he was almost relieved. He felt bad for setting up an honest man but a man who’d sold his soul wasn't allowed the luxury of compassion. He had only so many days left in his life and if he remained useful to Sam Winchester, he may earn himself a few more.

Sam called him and told him what to say to the detectives, what to say in court.

Ash did as he was told.


End file.
